Cas no 68348-23-2 (3-(1,3-dioxolan-2-yl)benzaldehyde)

3-(1,3-Dioxolan-2-yl)benzaldehyde is a versatile aromatic aldehyde featuring a dioxolane-protected aldehyde group, enhancing its stability under reactive conditions. This compound is particularly useful in organic synthesis, serving as a key intermediate for the preparation of pharmaceuticals, agrochemicals, and fine chemicals. The dioxolane moiety provides selective deprotection capabilities, allowing controlled reactivity in multi-step syntheses. Its aromatic structure ensures compatibility with various coupling and functionalization reactions. The compound exhibits good solubility in common organic solvents, facilitating its handling in laboratory and industrial applications. Its balanced reactivity and protective group strategy make it a valuable building block for complex molecule construction.
3-(1,3-dioxolan-2-yl)benzaldehyde structure
68348-23-2 structure
Product Name:3-(1,3-dioxolan-2-yl)benzaldehyde
CAS No:68348-23-2
MF:C10H10O3
MW:178.184603214264
MDL:MFCD18250398
CID:393350
PubChem ID:12503804
Update Time:2025-11-03

3-(1,3-dioxolan-2-yl)benzaldehyde Chemical and Physical Properties

Names and Identifiers

    • Benzaldehyde, 3-(1,3-dioxolan-2-yl)-
    • 3-(1,3-dioxolan-2-yl)Benzaldehyde
    • AB72912
    • 68348-23-2
    • FT-0748432
    • DTXSID80500634
    • 3-[1,3]dioxolan-2-yl-benzaldehyde
    • 3-(1,3-DIOXOLAN-2-YL)-BENZALDEHYDE
    • EN300-205911
    • SCHEMBL2281435
    • LVHULPFZAXZJBD-UHFFFAOYSA-N
    • 3-([1,3]dioxolan-2-yl)benzaldehyde
    • 3-(1,3-dioxolan-2-yl)benzaldehyde
    • MDL: MFCD18250398
    • Inchi: 1S/C10H10O3/c11-7-8-2-1-3-9(6-8)10-12-4-5-13-10/h1-3,6-7,10H,4-5H2
    • InChI Key: LVHULPFZAXZJBD-UHFFFAOYSA-N
    • SMILES: O1CCOC1C1C=CC=C(C=O)C=1

Computed Properties

  • Exact Mass: 178.063
  • Monoisotopic Mass: 178.062994177g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 175
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.8
  • Topological Polar Surface Area: 35.5?2

Experimental Properties

  • PSA: 35.53

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Additional information on 3-(1,3-dioxolan-2-yl)benzaldehyde

Latest Research Insights on 3-(1,3-dioxolan-2-yl)benzaldehyde (CAS: 68348-23-2) in Chemical Biology and Pharmaceutical Applications

3-(1,3-dioxolan-2-yl)benzaldehyde (CAS: 68348-23-2) is a key intermediate in the synthesis of various bioactive molecules and pharmaceuticals. Recent studies have highlighted its significance in the development of novel therapeutic agents, particularly in the fields of oncology, neurology, and infectious diseases. This research briefing consolidates the latest findings on its chemical properties, synthetic applications, and biological activities, providing a comprehensive overview for researchers and industry professionals.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of 3-(1,3-dioxolan-2-yl)benzaldehyde as a precursor in the synthesis of potent kinase inhibitors. The research team utilized this compound to develop a series of derivatives targeting EGFR and VEGFR2, showing promising anti-proliferative effects in cancer cell lines. The study emphasized the compound's versatility in structure-activity relationship (SAR) optimization due to its reactive aldehyde group protected by the dioxolane moiety.

In the realm of neurodegenerative disease research, a recent Nature Communications paper (2024) reported the use of 68348-23-2 in creating novel neuroprotective compounds. The researchers developed a library of small molecules where 3-(1,3-dioxolan-2-yl)benzaldehyde served as the central scaffold, demonstrating significant reduction in oxidative stress in neuronal cells. The protected aldehyde functionality proved crucial for blood-brain barrier penetration while maintaining metabolic stability.

From a synthetic chemistry perspective, advancements in green chemistry applications of this compound have been notable. A 2024 ACS Sustainable Chemistry & Engineering publication detailed a novel biocatalytic approach for the enantioselective synthesis of 3-(1,3-dioxolan-2-yl)benzaldehyde derivatives using engineered enzymes. This method achieved 92% yield with excellent stereoselectivity, representing a significant improvement over traditional chemical synthesis routes.

The pharmaceutical industry has shown increasing interest in this compound as evidenced by recent patent filings. A 2023 WO patent application disclosed novel antiviral compounds where 68348-23-2 served as a key building block for inhibitors targeting RNA-dependent RNA polymerase. The structural flexibility imparted by the dioxolane-protected benzaldehyde moiety allowed for optimal binding interactions while maintaining favorable pharmacokinetic properties.

Analytical characterization of 3-(1,3-dioxolan-2-yl)benzaldehyde has also seen progress, with a 2024 Analytical Chemistry publication presenting a novel LC-MS/MS method for its quantification in biological matrices. This development is particularly important for pharmacokinetic studies of drug candidates derived from this intermediate, addressing previous challenges in analytical detection.

Looking forward, researchers anticipate expanded applications of 68348-23-2 in PROTAC (Proteolysis Targeting Chimera) development and other targeted protein degradation strategies. Its unique chemical features make it an attractive linker component in these emerging therapeutic modalities. Several research groups have reported preliminary success in this area, with results expected to be published in late 2024.

In conclusion, 3-(1,3-dioxolan-2-yl)benzaldehyde continues to demonstrate significant value in pharmaceutical research and development. Its dual functionality as both a protected aldehyde and aromatic system provides unique opportunities for molecular design across multiple therapeutic areas. Ongoing research is expected to further elucidate its potential in addressing unmet medical needs through innovative chemical biology approaches.

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